The first entry to pyrrolo[2,3- c ]quinoline-2,4(3a H ,5 H )-diones

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Tetrahedron, ISSN: 0040-4020, Vol: 64, Issue: 19, Page: 4387-4402

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10.1016/j.carbpol.2007.07.001, 10.1016/j.tet.2008.02.063
Kafka, Stanislav, Klásek, Antonín, Polis, Jiří, Rosenbreierová, Veronika, Palík, Ctirad, Mrkvička, Vladimír, Košmrlj, Janez
Elsevier BV, Pergamon Elsevier Science Ltd.
Materials Science, Chemistry, Biochemistry, Genetics and Molecular Biology, Pharmacology, Toxicology and Pharmaceutics, pyrrolo[2,3-c]chinolony, chinolinony, Wittigova olefinace, mechanismus, NMR, Pyrrolo[2,3-c]quinolones, Quinolinones, Wittig olefination, Mechanism, vyfukování, mechanické vlastnosti, plasikátor, škrob, termoplastický škrob, film blowing, mechanical properties, plasticizer, starch, thermoplastic starch
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Wittig olefination of 3-aminoquinoline-2,4(1 H,3 H )-diones 1 with ethyl (triphenylphosphoranylidene)acetate (Ph 3 P CHCO 2 Et) afforded ( E )-3-amino-4-ethoxycarbonylmethylene-1,2,3,4-tetrahydro-2-quinolones ( E )- 2 and pyrrolo[2,3- c ]quinoline-2,4(3a H,5 H )-diones 3. An alternative approach for the synthesis of 3 via 3-bromoacetamidoquinoline-2,4(1 H,3 H )-diones 7, their corresponding triphenylphosphonium salts 8, and ylides A that undergo intramolecular Wittig reaction, was investigated. Under the applied reaction conditions, the phosphonium salts 8 and ylides A are so unstable that they partly decompose to 3-acetamidoquinoline-2,4(1 H,3 H )-diones 9 during the synthesis of 3.

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